Some Constituents of the Poison Ivy Plant (Rhus Toxicodendron)Syme, William Anderson
Science
Some Constituents of the Poison Ivy Plant (Rhus Toxicodendron)
Syme, William Anderson
Poison ivy
A portion of the poisonous tar was heated in an open dish with strong
acetic acid. The tar seemed to be decomposed to some extent, giving a
yellow substance. Acetic acid was added from time to time as it
evaporated. After several evaporations, water was added, the mixture was
heated to boiling and filtered. This filtrate No. 1 will be mentioned
later. The residue in the dish consisted of undecomposed tar and an
olive-green flaky substance. This substance was heated with a fresh
portion of glacial acetic acid. Water was added, and the mixture was
boiled and filtered. The filtrate had a deep yellow color suggesting
fisetin. It was shaken out with ethyl acetate which became colored
yellow. A portion of the ethyl acetate solution gave an orange red
precipitate with lead acetate showing the presence of fisetin. The ethyl
acetate was removed from the remainder of the solution by evaporation
and the yellow residue was taken up in alcohol. This alcoholic solution
gave the characteristic reactions for fisetin with stannous chloride,
with potassium hydroxide, with ferric chloride and with Fehling
solution.
Filtrate No. 1 obtained by heating the poisonous tar with acetic acid
and hot water as described above was investigated as follows: A portion
of it gave a reddish colored precipitate with sodium carbonate as in the
case when the tar was hydrolyzed with sulphuric acid. The remainder was
nearly neutralized with sodium carbonate and lead acetate was added in
excess to remove gallic acid. The excess of lead was removed by
sulphuric acid, and the sulphuric acid was removed by barium carbonate.
The solution on evaporation reduced Fehling solution to some extent, but
a white precipitate was also formed.
In this experiment, gallic acid and fisetin and probably sugar were
formed by decomposition of the poisonous gum with acetic acid, the acid
found in the plant by Pfaff. The presence of free gallic acid, fisetin
and rhamnose in the plant can therefore be explained by the natural
hydrolysis of a complex gum or tar or a constituent thereof. The
poisonous property is lost in the general rearrangement which takes
place during hydrolysis.
The poisonous tar was not hydrolyzed by boiling with a dilute solution
of sodium carbonate.
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